Hero of Waterloo – The Rocks / Millers Point

The last time I went to the Hero of Waterloo it was on a first date with a woman who had a particularly deep and plunging cleavage. As we tried to get to know each other a man interrupted, peered intently into my date’s bosom, and then turned to me.

“You better be careful with this one, mate,” he slurred. “A man could get lost in there!”

Which was wildly out of line (although I was planning on doing just that) and yet also oddly appropriate, as legend has it that in Sydney’s early days many a man did disappear in this very pub.

Apparently there used to be a tunnel that led from the pub’s cellars to the ocean (I’ve been told it’s since been blocked off) that was used for rum smuggling. However, the myth goes that the tunnel was also used to drag drunks who’d passed out in the pub onto ships, meaning that when they woke up they’d find themselves with both a hangover and a new career as an unwitting sailor.

Whether this tale is true or not is another story, but as I pop back in on a Sunday afternoon and order a James Squire porter from the bartender, I can’t help but wonder if he’d sell me to a ship’s captain too if given half a chance. I pay for my beer suspiciously and make a pledge to myself not to pass out here.

The atmosphere is casual and lively, with a jazz band playing on a tiny stage next to a fireplace and a group of what seems to be locals out for a good time.

The main attraction is that the bar doesn’t seem to have changed much over the decades – or should we say centuries, since it opened in 1843. From its sandstone walls and wooden beams to the uncomfortable church-style pew against one wall, this genuinely feels like an old pub (if you ignore the pokies standing forlornly on one side of the bar).

You can also get meals here, such as burgers, steaks and fish and chips, which can be eaten in a separate dining room.

It’s hard to beat the Hero of Waterloo when it comes to history and atmosphere, and it can get lively when there are bands on (usually from Wednesdays to Sundays, with the genre ranging from Irish folk to jazz). You might, however, want to think twice before taking a buxom date here – or before passing out.